My Todo app (Remember the Milk) reminds me each month to download (to Moneydance) and record all the Vanguard transactions. I usually put it off, and do it every few months because it's a hassle.
The main problem is that using VanguardAdvantage to pay most of my bills means that every transaction involves a "Sweep to brokerage" (from the money market) and a payment. I have to refer to my notes to remember how to do this (see below).
Since the return on the MM is so low these days, I thought I could save myself some of this hassle by paying bills from my regular old checking account, replenishing it from the MM periodically. Thus there would be only one transaction per bill payment.
1. Sound like a good plan?
2. Any other ideas for reducing the processing load?
My notes concerning the VG downloads:
In the Prime MM, you'll see a sell transaction (Description SWEEP TO BROKERAGE). Just change the category to nothing, and Confirm the transaction.
On the VanguardAdvantage side, you'll see an Xfr transaction with a positive value. Change the "Transfer" category to "Prime MM Normal" and Confirm it.
Do the above for all of the positive values. Then view only the unconfirmed transactions. They should all be negative. Fill in the payee and category (For example, set payee to "Mastercard Payment" and the Transfer to "Mastercard." Or, for example, change it to Farmer's Insurance and the category to "Car:Echo:Insurance"), and confirm.
After doing this, go to the mastercard account and you should be able to merge the payments with existing transactions.
You can view or print all of the Billpay transactions, and then go through them and set the correct payees. Tags are not implemented here.
Check that the cash balance is zero. If not, find the place where it stops "returning to zero" after every few transactions.